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CHEBI:65856 - 5α-epoxyalantolactone

ChEBI IDCHEBI:65856
ChEBI Name5α-epoxyalantolactone
Stars
ASCII Name5alpha-epoxyalantolactone
DefinitionA sesquiterpene lactone that is the 5α-epoxy derivative of alantolactone. Isolated from the root extracts of Inula helenium, it exhibits antimycobacterial activity.
Last Modified21 January 2013
DownloadsMolfile
FormulaC15H20O3
Net Charge0
Average Mass248.322
Monoisotopic Mass248.14124
SMILES[H][C@@]12C[C@@]3(C)CCC[C@H](C)[C@@]34O[C@H]4[C@]1([H])C(=C)C(=O)O2
InChIInChI=1S/C15H20O3/c1-8-5-4-6-14(3)7-10-11(9(2)13(16)17-10)12-15(8,14)18-12/h8,10-12H,2,4-7H2,1,3H3/t8-,10+,11+,12-,14+,15-/m0/s1
InChIKeyYIQKVCDNUFDAHB-HKKVUVRFSA-N
Species of MetaboliteComponentSourceComments
Inula helenium (ncbitaxon:55635) root (BTO:0001188) PubMed (10364842)
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimycobacterial drug  A drug used to treat or prevent infections caused by Mycobacteria, a genus of actinobacteria. Aerobic and nonmotile, members of the genus include the pathogens responsible for causing tuberculosis and leprosy.
Application:
antimycobacterial drug  A drug used to treat or prevent infections caused by Mycobacteria, a genus of actinobacteria. Aerobic and nonmotile, members of the genus include the pathogens responsible for causing tuberculosis and leprosy.
ChEBI Ontology
Outgoing Relation(s)
5α-epoxyalantolactone (CHEBI:65856) has functional parent alantolactone (CHEBI:2540)
5α-epoxyalantolactone (CHEBI:65856) has role antimycobacterial drug (CHEBI:64912)
5α-epoxyalantolactone (CHEBI:65856) has role metabolite (CHEBI:25212)
5α-epoxyalantolactone (CHEBI:65856) is a epoxide (CHEBI:32955)
5α-epoxyalantolactone (CHEBI:65856) is a naphthofuran (CHEBI:39270)
5α-epoxyalantolactone (CHEBI:65856) is a sesquiterpene lactone (CHEBI:37667)
IUPAC Name 
(1aR,2S,5aR,6aR,9aR,9bS)-2,5a-dimethyl-9-methylideneoctahydro-2H-oxireno[4,4a]naphtho[2,3-b]furan-8(9H)-one
Registry NumbersSources
Reaxys:5031399Reaxys
Citations